Engineering Manager (Developer Tooling)

Headway is building a new mental healthcare system that everyone can access by making it easy for therapists to accept insurance and scale their practice.  Headway was founded in 2019. Since then, we’ve grown into a diverse, national network of over 60,000 mental healthcare providers across all 50 states who run their practice on our software and have served over 1 million patients. We’re a Series D company with over $325m in funding from a16z (Andreessen Horowitz), Accel, GV (formerly Google Ventures), Spark Capital, Thrive Capital, Forerunner Ventures and Health Care Service Corporation. We want your time here to be the most meaningful experience of your career. Join us, and help change mental healthcare for the better. About the Developer Tooling team at Headway (Engineering Foundations) The Developer Tooling team is part of Engineering Foundations at Headway. Engineering Foundations builds the core platforms, infrastructure, and AI-driven development systems that enable all engineers to build, test, deploy, and operate software with speed and reliability. Developer Tooling focuses specifically on the day-to-day developer experience. Our customers are Headway’s engineers. We own the systems and workflows that directly impact developer velocity, confidence, and code quality, including CI/CD, test infrastructure, local development environments, observability, documentation tooling, and AI-powered developer workflows. Our goal is simple and high impact. Reduce friction in the development lifecycle so engineers can spend less time dealing with flaky tests, broken environments, and opaque pipelines, and more time shipping high-quality product experiences for patients and providers. Principles that guide us Developer experience is a product. Internal tooling is treated with the same care and quality bar as customer-facing software. Stability enables speed. Predictable pipelines and reliable feedback loops are prerequisites for velocity. Automation over toil. Repetitive or manual work should be automated wherever possible. Thoughtful AI adoption. AI is used to expand what engineers can do, not to replace judgment or craftsmanship. Clear ownership. Reliable systems require explicit ownership, accountability, and fast feedback loops. About this role As Engineering Manager for Developer Tooling, you will lead a team responsible for the core developer experience at Headway. You will own strategy and execution for tooling and systems that every engineer relies on to build, test, and ship software. A major focus of this role is advancing AI-powered developer productivity. You will help define how AI is used across engineering, from inner-loop coding assistance to agentic workflows for planning, testing, refactoring, documentation, and troubleshooting. This role is about enabling engineers to work more effectively at scale by making AI a trusted, integrated part of the development workflow. You will operate within Engineering Foundations and partner closely with product engineering leaders and other platform teams. You will run tight feedback loops with the engineering organization, translate developer pain into durable improvements, and set clear standards for reliability, quality, and usability across shared tooling.   Who you are A people-first engineering leader who cares deeply about developer experience Technically credible and comfortable going deep on CI/CD, test systems, and developer tooling AI-forward with hands-on experience using modern AI-assisted development tools Pragmatic and outcome-oriented, with a bias toward shipping improvements that engineers feel quickly A clear communicator who can align stakeholders and advocate effectively for platform investments Experience we’re seeking 3+ years of experience managing software engineering teams Experience owning developer tooling, platform infrastructure, or internal engineering systems Strong understanding of CI/CD, test reliability, and local development workflows Hands-on experience with AI-powered developer tools and interest in agentic workflows Track record of improving developer velocity, reliability, or code quality at scale Experience partnering with product engineering teams as internal customers You’ll love this role if you want to Shape how engineers across the company build software every day Lead the adoption of AI as a first-class part of the development workflow Eliminate flaky tests, unreliable CI, and broken local environments Build tooling that compounds in value as the organization scales Combine technical depth, people leadership, and org-level impact in a single role Compensation and Benefits: The expected base pay range for this position is $198,000-$237,500, based on a variety of factors including qualifications, experience, and geographic location. In addition to base salary, this role may be eligible for an equity grant, depending on the position and level. We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation: decisions are made holistically, ensuring fairness and alignment with market benchmarks while recognizing individual contributions and potential. Benefits: offered include: Equity compensation Medical, Dental, and Vision coverage HSA / FSA 401K Work-from-Home Stipend Therapy Reimbursement 16-week parental leave for eligible employees Carrot Fertility annual reimbursement and membership 13 paid holidays each year as well as a Holiday Break during the week between December 25th and December 31st Flexible PTO Employee Assistance Program (EAP) Training and professional development We believe a team's strength is in its people, and we cannot achieve this mission without a team that reflects the diversity of this problem – across race, ethnicity, gender, sexuality, age, national origin, religion, family status, disability, military status, and experience. Headway is committed to the full inclusion of all qualified individuals. As part of this commitment, Headway will ensure that persons with disabilities are provided with reasonable accommodations. If reasonable accommodation is needed to participate in the job application or interview process, to perform essential job functions, and/or receive other benefits and privileges of employment, please inform the recruiter when they contact you to schedule your interview. Headway participates in E-Verify. To learn more, click here. A notice to Headway applicants: To protect yourself against phishing and recruitment fraud, please note that Headway only accepts applications through our official careers page at https://headway.co/careers. Headway will never refer you to external websites, ask for payment or personal information, or conduct interviews via messaging apps. All official communication will come from a @findheadway.com email address. If you are contacted by someone claiming to be from Headway via an unofficial channel, please do not share any information and report it as spam.